Regrets as Guideposts

One of the reasons I was hesitant to start this newsletter was due to concerns about writing something I would disagree with in future. This post is probably one of those but here it goes.

We live in a society that espouses “no regrets”. Yet regrets are a near universal experience. Regrets are interesting because they are both backward and forward looking. We regret something we did, or in most cases, didn’t do. We compare the outcome to a time before that decision was made. Sometimes we compare the outcome to a fantasy. An alternative path that exists nowhere but our minds. Examining what we regret and why we regret it can help prevent future regrets, not just in terms of avoiding repeating the mistakes of the past, but also in shaping how we live in the future.

Regrets can act as guides, pointing to our values, desires and dreams, even if we don’t know or acknowledge these in everyday life.

There are two books on this topic which have made some waves in pop culture: Daniel Pink’s, The Power of Regret (or what I like to refer to as the regrets of the living) and Bronnie Ware’s, The Regrets of the Dying. Pink’s World Regrets Survey gathered over 18,000 responses, most of which aligned with four categories. Some of these overlapped with the five most common regrets shared with Ware during her work as a palliative carer.

Unsurprisingly, the dying don’t seem to focus on foundation regrets. Not maxing out your tax deductible pension contribution doesn’t quite carry the same weight at that stage…

Foundations are important. Particularly taking care of your health. We all know that. Doing things that bring stability in your life such as building a nest-egg of savings is valuable both in terms of protecting you from unexpected setbacks, and for freeing your mind to focus on things that truly matter instead. However, focusing too much on foundations can come at a cost. It can cause us to not pursue ideas that later become boldness regrets. It can lead us to building solid financial and well-credentialed foundations under a life we hate living. 

I’m not a life coach. I certainly don’t have my sh*t figured out enough to give anyone unquestionable advice, so question all of what I’m about to say. 

As someone who is at a crossroads careerwise, I’ve been thinking a lot about the role of work in shaping my life. One of the common regrets people have at the end of their lives is, “I wish I hadn’t worked so hard”. In her book, Ware highlights that people “regretted spending so much of their lives on the treadmill of a work existence.” I probably haven’t yet fully understood the wisdom of that statement but as someone who has reached ~40% of my average life expectancy (a truly terrifying thought), my interpretation is that people regret letting work dictate the terms of their life, allowing their time to be spent on things that didn’t matter greatly (Slide decks! Quarterly projections! Performance reviews!) at the expense of things that did (dinners with family, time with friends, doing things that brought them joy no matter how frivolous). Contrast this regret with those still in the midst of living. Many people seem to have foundation regrets about not working hard enough to get them to where they want to be. Many also have boldness regrets related to work such as not seizing the opportunity to have their Emily in Paris moment by taking a posting abroad. Perhaps these regrets will seem trivial on our deathbeds but the reality for most of us is that work is a necessity and a powerful force in shaping the quality of our everyday lives. It’s easy to be cynical about work but I’m a big believer that our work (not necessarily always our jobs but rather what we choose to pour ourselves into) can be an enormous source of fulfilment. A vehicle for growth. A net positive for society. Of course a lot of work is bullsh*t, a complete waste of time and talent. I’m not here to tell anyone how to live their life but I do think it’s important to try to seek out a career path that enhances your life in the ways that matter most to you. Derek Thompson expresses this perfectly in his brilliant essay, Your Career Is Just One-Eighth Of Your Life:

Work is too big a thing to not take seriously. But it is too small a thing to take too seriously. Your work is one-sixth of your waking existence. Your career is not your life. Behave accordingly.

Work being one-sixth of your waking existence is not a given. Some of us will have much less time. Like many of you reading, I’ve had family members pass away long before their retirement years. It’s something I’ve been thinking a lot about recently. I wish I could say it has cultivated a need for me to seize every day (that’s still a work in progress). It has made me acutely aware of the impact time-frames have on my decisions. I could live to be 106. I could die tomorrow. How I’d choose to spend my time, and with that my career, drastically differs if I knew I had 1 year to live versus 20 or 60. My regrets will be accentuated by a lifespan I have no prior knowledge of, and limited control over. 

I’m not sure what this all means for how I should live my life. The best I’ve come up with so far is this » Try to live life in a way that optimises for the very short term and long term each day. Stop to smell the proverbial roses and find little moments of joy in each day. Work towards the things that you have relatively high conviction will matter to you in the long term and try not to screw your future self over in the process. If you’re lucky enough to know your dreams or what truly matters to you, pursue those now. Act as if there isn’t enough time. This doesn’t necessarily mean upending your life entirely, although it might if that feels right. Aim to live a life that minimises regrets not just risks. 

I don’t think everyone should spend all their days dwelling on regrets. That seems like an utter waste of the precious life we’ve been given. However, examining our regrets every now and then can help to act as guideposts to redirect our lives if needed. Here are a few prompts which may be helpful:

• Review the regrets listed above. Which resonates? Why? Is it signalling a change is needed? If yes, when do you plan to act on it?

• What do you regret most about the past year? Are there any you can rectify? How can you prevent these from occurring again in the future? 

• What do you think you’ll regret not doing in the next year? In the next 5 years? Do these truly matter to you or are they things you feel you should do? If they do matter, how can you get started? 

Once you have compiled your list of regrets, as a counterbalance, I recommend reading this beautiful excerpt from Matt Haig’s The Midnight Library, and embrace his version of “no regrets”.

“It is easy to mourn the lives we aren't living. Easy to wish we'd developed other other talents, said yes to different offers. Easy to wish we'd worked harder, loved better, handled our finances more astutely, been more popular, stayed in the band, gone to Australia, said yes to the coffee or done more bloody yoga.

It takes no effort to miss the friends we didn't make and the work we didn't do the people we didn't do and the people we didn't marry and the children we didn't have. It is not difficult to see yourself through the lens of other people, and to wish you were all the different kaleidoscopic versions of you they wanted you to be. It is easy to regret, and keep regretting, ad infinitum, until our time runs out.

But it is not lives we regret not living that are the real problem. It is the regret itself. It's the regret that makes us shrivel and wither and feel like our own and other people's worst enemy.

We can't tell if any of those other versions would of been better or worse. Those lives are happening, it is true, but you are happening as well, and that is the happening we have to focus on.”